


One Shot To Many

by allhewantsispie, IAmSherloved7043



Series: Role Plays [2]
Category: Supernatural
Genre: Alcohol Abuse/Alcoholism, Anal, Ball Gags, Begging, Blindfolds, Blow Jobs, Bottom Dean, Bottom Dean Winchester, Butt Plugs, Cock Rings, Confessions, Daddy Kink, Dildos, Dirty Talk, Dom/sub Undertones, Drunk Sam, Drunk Sam Winchester, First Time, Gags, Incest Kink, M/M, Manhandling, Name Calling, Oral, Oral Sex, Orgasm Control, Orgasm Delay, Orgasm Delay/Denial, Orgasm Denial, Power Bottom Dean, Power Bottom Dean Winchester, Praise Kink, Requited Love, Riding Crops, Rough Sex, Stripper, Strippers & Strip Clubs, Top Sam, Top Sam Winchester, UST, Whips, Wincest - Freeform, angust, dildo, mentioned dean winchester/original femail character, strip club
Language: English
Status: Completed
Published: 2016-08-05
Updated: 2016-08-05
Packaged: 2018-07-29 12:43:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,179
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7684954
Author URL: https://archiveofourown.org/users/allhewantsispie/pseuds/allhewantsispie, https://archiveofourown.org/users/IAmSherloved7043/pseuds/IAmSherloved7043
Summary: <blockquote class="userstuff">
              <p>Dean takes Sam to a strip club after a hunt. Sam can't stand to see his big brother constantly with other woman, so he gets a little too drunk (very drunk) and lets a few secrets slip. Dean does not mind~</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Hey guyz so this is another rp that i am wotking on! Me and the other person haven't finished yet so give us some time. I will be addng the rest of what we have so far later. Comment prompts!

Dean waited in the impala outside of the crappy pawn shop, Sam came out, wiping the demon blood on the knife on his jacket and then giving me a small smile, hiding it in his inner pocket and coming to the other side of the Impala and closing the door, sighing, "So, how'd it go, how many were there in there?" Dean asked, voice still husky since it was 5am and he only just woke up around 30 minutes ago  
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Flashbacks of a few moments ago passed in Sam's head. He had gone in expecting 1 or 2 demons and was presented with 4. It was tough, but Sam was big and strong enough to handle himself. Less than 10 minutes after he entered he walked back out, barely a scratch on him. "4, easy 'nuff." Sam was almost bored of the routine: research, travel, kill, bar and restart. Sometimes he just wanted to relax and take things slow. "Back to the motel?" he asked, knowing well that Dean almost always got piss drunk after hunts.  
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"Nah I think i'll hit the bar, maybe get a little action" Dean smirked, chuckling, "You can go back in you want, find the next hunt" Dean suggested, starting the car  
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"I'll- I'll go with you." Sam frowned slightly. If he had to see Dean chase after some tail he would like to be piss drunk. For years he had to hear Dean with other people, other /woman/, when Sam was right there. Of course, Dean didn't know this. /He would think i was a freak/ Sam thought. Sometimes he couldn't help but wonder 'What if?' /If i eased Dean into the idea, maybe, just maybe/  
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"Okie Dokie" Dean drove to the nearest strip club and got out of his Baby. Stepping into the strip club he looked around at all the girls dancing gracefully on the poles, "Oh yeah" Dean said, smiling, he turned to Sam and gave him $200 and smiled, "Go treat yourself"  
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"To a beer." Sam said sarcastically,   handing Dean back most of the money. Getting hammered was top priority in Sam's head  
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"Okay then I guess i'll treat myself" He walked away from Sam and to one of the strippers, sitting down right in front of her, he smiled, this girl was amazing, a natural. She slid down and got onto her knees, she leaned towards Dean and lifted his chin with 2 fingers, whispering, "Come to the back with me baby" Dean smiled widly, "Anything for you, beautiful"  
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/Fuck no. I am not drunk enough for this shit yet. Seriously Dean? Two fucking minutes?/ Sam thought to himself. While he was dissing Dean for his quick actions, Sam was already on his forth shot of the strongest drink they had. He had begun to feel a bit tipsy but called for another 2.   
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Dean gets dragged into a small bedroom in the back and he takes off his shoes and jacket, then overshirt then a t-shirt and gets pushed onto the bed, he watches as the girl takes off her heels and black tights , climbing onto the bed and on top of Dean as he bites his lip, smiling, "Holy mother of God" He says as she takes her bra off, revealing two bouncing beauties   
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Not 10 minutes later Sam, who could barely walk or see straight, wobbled to the Impala, leaning against it waiting for Dean. Sam started thinking after a while. /Dean's in there, fucking some random slut, watching her blow him and ride him when it could be me. Goes through all thise girls and his own fucking brother can't even get a turn./ Sam knew Dean never even expressed any sort of attraction to guys, nevermind his brother. /Should go in there right now. Kick that whore out, show Dean who really matters./ In his drunken state it sounded like a perfect plan. And that's what he re-entered the club to do  
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Dean wobbled out of the room, clothes not buttoned properly, hair all messed up and breathing heavily, he chuckled, "that was amazing" The girl waved and went back on stage, he saw Sam and started walking up to him "Dude she gave THE best blowjobs"  
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Upset that he missed his moment, Sam mumbled out an annoyed "Fuck her. I could do better." under his breath. Although mad, Drunk Sammy also had a small boner seeing Dean all messed up and ruffled  
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Dean blushes, "What?" He said, giving his /what the fuck do you think you're talking about/ look, "Dude I think you're definately too drunk"  
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Sam turned around after trying, and failing, to shove Dean 'playfully'. "I didn' say nontin'" he grumbled out. "Just- get in te' car n' drive De." Walking out he tripped, over nothing, and fell to the floor, his huge body creating an 'Umph!' sound upon landing  
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"Yeah okay definately too drunk" Dean picked up Sam and walked him to the car, sitting him in shotgun and driving back to the motel  
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Sam was still sulking, never really stopped. " 'tupid idea anywa'. Shoulda stayed 'ome. Hate wachin' you." This was the reason Sam never got drunk, no filter to what he says.  
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"W-What do you mean you hate watching me? Hate watching me do what?" Dean asked, continueing to drive  
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Sam ignored him, falling asleep until they got back to the motel. Once there Sam stumbled to the door. He had sobered up a bit during his sleep so he unlocked the door using a small bit of effort. "I nee' sleep. An' food. We got any food De?" He asked, mind still fuzzy  
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"Uh yeah theres um some pot noodles in the cupboard" Dean said, taking his jacket off and putting it on the back on the closest chair, "Are you sure you didnt say anything earlier?"  
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Sam remembered perfectly, but a part of gis mind didn't want to admit it to his brother. "Uhh~" he staled. Clearing his throat he continued, "N-no! What're you talking about Dean? I did-didn't say anyth-thing" He turned around, awkwardly shifting things in the small kitchen  
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"Are you" Dean walked up behind him and breathed into his ear, "Absolutely sure?" He smirked, knowing exactly what Sam had said earlier  
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Sam let out a shakey breath. Their proximy and the alcohol level in his blood made Sam harden up. /Fuck, not now!/ he begged in his mind, closing his eyes trying to repress it. "You wouldn't understand Dean. Just drop it okay?"  
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Dean sighed then turned Sam around and stared into his eyes, "Fine." He said, walking away and laying on one of the beds, closing his eyes, as he was turning away his hand brushed Sam's hard-on, he tried to forget about it but eventually got fed up and stood up, "Goddammit Sam"  
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Sam sat up quickly at the sound of his name. "What is it Dean?! What's wrong?!" He stood up and walked over to his big brother, noticing nothing was physically wrong anywhere. He gulped. "Dean?"  
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Dean turned to him angrily and kissed him viciously, grabbing the back of his head with one hand and pulling him closer by his jip with the other, after nearly fainting from the lack of air, Dean separated, "Does that explain it?" He said as if he was talking to a child  
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Sam kissed Dean back once he realized what was happening. He laced his arms around Dean's neck, holding him close. When they seperated Sam caught his breath. "Fuck, Dean I- you- you weren't supposed to know~ fuck" He pulled Dean back in for another kiss, harder and filled with lust and want.  
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Dean smirked through the kiss, grabbing Sam's ass firmly and pulling at his hair. Dean turned them around and pinned Sam against the nearest wall, chuckling, "You're a needy little whore aren't you? Wanting some action from your own brother?" Dean whispered into his ear, biting down on it slightly  
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Sam grunted hitting the wall, he loved being manhandled but never would let Dean know. He took his chance and rubbed his growing erection on the wall, breathing hard. "Fuck! Yes Dean. God!- Yes! I'm a needy slut I need- your cock Dean please! Spank my ass! Use me~"   
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Dean grew harder as Sam dirty talked him, "Never knew I had such a slut of a brother" Dean started grinding against Sam's ass, "You like that don't you though? Being a slut, getting your big brother to grind against your pretty little ass, you love it, don't you Sammy?" Dean said, biting down on Sam's shoulder hard and then sucking on it, "Do you wanna suck on your big brother's cock Sammy? Be a fucking whore for your big brother? Deepthroat his fucking cock until you gag?"   
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Sam was sure if Dean wasn't holding him up he would fall to the floor. He was so hard it fucking /hurt/, and Dean's dirty words only made it worse. "Love being a- a slut. Only for you Dean. Only a fucking whore for you. Love it-Fuck! yesss~. I'm your fucking slut!" Sam felt needy as he moaned like a whore, still trying to find friction anywhere he could. "Please! Please Dean- Mmmhn!- "  
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Dean grabbed Sam's hair roughly and pushed him down so he was staring at his clothed cock, "Suck my cock little brother until you're begging for mercy and until you're gagging over and over again" Dean ordered, unzipping his pants and pulling down his boxers, revieling his 8-inch cock


	2. Chapter 2

Sam winced at the pain of being controlled by his hair but loved the pleasure it sent to his cock, loved the way he was simply being /used/. He wasted little time opening Dean's pants. He's wanted this for so long, longer than he remembers and now Dean is right /there/. Ordering Sam around like he owns him. Sam isn't complaining. He started teasing Dean through his boxers with his tounge keeping eye contact with his big brother, seeing how worked up he could get.  
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"Sam" He said roughly, "No teasing, suck my fucking cock or i'll punish you" He said, yanking his head upwards so he would look at Dean, "Understood?"  
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Sam instinctively moved to grab Dean's arm. His other hand continued to lightly rub over Dean's coverd dick. "Is that a promise De?" Sam smirked.  
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Dean whimpered slightly at the touch, "Yes, Sammy, it is. So how about you get your mouth working on my cock already, im getting impatient"  
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"Of course" Sam pulled down Dean's boxers, holding his hard 8 inches before taking most of it, about halfway, before he started to gag. He worked his tounge over the head, moving down his shaft while sucking perfectly, all while still maintaining eye contact. He loved the expressions Dean made because Sam is making him look like that.  
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"Go to the bottom" Dean said, "If you can't make it all the way down, and I mean nose-touching-my-pubic-hair all the way down, I will have to do it myself, okay Sammy?"  
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Sam tried his best to force his way to the bottom, he really did. He was gaging and almost crying by the time he just had to pull off before he passed out. "I'm-I'm sorry ~"  
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Dean smirked, "Guess i'll have to do it myself" Dean grabbed a handful of Sam's hair and pulled his face towards his cock, "If you pass out, we're never doing this again, understand me, Sammy?" He forcefully face-fucked Sam all the way down and all the way up, his gagging was turning Dean on, Dean knew Sam belonged to him, so seeing him so vunruble was a big turn on  
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Sam began to tear up, partly because of the face fucking Dean was doing and partly because he did not want to lose Dean. He waited so long for this and now he could not let it slide away. He tried as hard as possible to suck Dean but it seemed difficult as he was thrusting into Sam's mouth with a punishing force.  
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Dean slowly pulled out of Sam's wet (and pleasing) mouth and watched as he tried to get his breathing pattern normal, he stared at him, smiled and ruffled his hair, "Good job Sammy"  
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Sam fell to the ground, taking deep breaths and coughing. "De-Dean~" he moaned  
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"Yes Sammy? What do you want?" Dean gets down on his knees and picks up Sam's chin, looking him in the eye and tilting his head he says, "Do you want your big brother cock?"  
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"Ye-yes. Please De? Please will you fuck me Dean? Make me yours, slap my ass, make me cum~" Sam begged. He lifted his head to place several short kisses all over his big brother's face and neck  
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"First" Dean says, standing up, "You have to prove how much of a cock slut you are, what would you do for my cock, Sammy?" Dean bent forward, whispering into Sam's ear, "What would you do to have my fat cock in that gorgeous ass of yours, huh Sammy?"  
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Sam let out a loud moan. He loved the way Dean could make him hard with his words and control him with a simple action. After all, Sam belonged to him. He didn't doubt that for even a second. He got on his knees, holding Dean's thighs while begging for his cock."I'm your slut Dean, your pet- fuck, I'll do anything for you! Only do what you say, I'll be a such good boy for you. I'll worship you if you want! Mmmhn, Dean, let you hurt me, call me your slut cuz' i am. Please! Oh shit- please- fuck Daddy~"  
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Dean smirked, "Perfect" He said, helping Sam up, "Get on the bed, lay down on your back and spread yourself for me and let me see that hole of yours, ill be there in a minute"  
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Sam did as he was told, not wanting to break his promises to Dean. " De? Where are you going? Please don't leave me here alone, I'm so hard De!" Sam pleaded when he noticed Dean was leaving.  
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Dean heard Sam and turned back, "Dont worry Sammy, im just getting some toys, also, don't touch yourself" Dean walked to the kitchen and opened one of the cabinets, he took out a leather riding crop, some handcuffs, a blindfold, a gag, a dildo and a buttplug.

**Notes for the Chapter:**

> comment prompts!


	3. Chapter 3

Sam writhed on the bed, desperate for friction. He tried everything from shaking his hips to pulling together his thighs to almost allowing himself to hump a pillow. Soon enough he was sweating and calling out his Daddy's name quietly, silently begging to cum. Not knowing what to do with his hands, he refrained from rubbing his cock by gripping the headboard as tight as he could. It didn't help much, he was still moaning like a whore when Dean came back  
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Dean watched as Sam writhed around the bed, hungry for friction, "Ive got them" Dean says, putting the items down on s nearby chair, "Now get undressed"  
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Sam's eyes widened when he saw the toys. Weither it was in fear or excitement of what Dean was going to to him was unknown. "D-Daddy?" he asked, fully undressed, hard cock throbbing against his stomach.  
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Dean walked up to Sam holding the blindfold, gag and handcuffs, "Lay down on your back" He ordered, walking up to the bed slowly  
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Sam slowly backed up, easing himself on the bed. He didn't take his eyes off his new toys, couldn't even if he wanted to. He would be conpleatly at Dean's mercy, and that thought alone made him make an inhuman moan  
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"Arms up" Dean said, cuffing both hands to the headboard, "You're such a good boy today Sammy, aren't you?"  
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"Yes Dean~" Sam swalllowed. "Promised you didn't I?" He tugged on the handcuffs to remind himself that he was trapped, loving all the feeling pouring into him and heading straight dor his cock. "Please De, please give your good boy what he wants" he added seductively  
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"Of course" He smiled, putting the gag on, "Anything for my good little boy" He put the blindfold on, seeing Sam so out-of-control and totally submissive was a big turn-on for Dean, Sam was a big guy, hell, he could probably take 8 guys on at once and win, but that was a totally different story in bed.  
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Sam whined at the blondfold, wanting to watch Dean. "N-no! Please Dean, need to see you!" He begged, but somewhere he knew his big brother wasn't going to comply. Sam knew he was Dean's little toy, and Dean could do anything he wished  
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"Shhhh" Dean said, tightening the gag more. He leaned forward next to Sam's ear and whispered, "You're my little toy, so don't cum until I tell you to, if you do, im going to have to punish you, m'kay?" Dean smirked and kissed down Sam's jawline, he then moved down, creating many hickies all around Sam's neck and shoulders, "You're my little whore~" Dean sang, licking Sam's left nipple lightly, "My little brother is a slut" Dean said, "A slut for his own big brother" He moved on the the right nipple, both his hands on Sam's hips, "My little brother is a boy toy" He placed kisses all around Sam's chest, casually licking his nipples on the way, "My boy toy"  
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Sam couldn't talk, as much as he wanted to the gag prevented any attempt to talk. So Sam moaned and nodded his agreements. /How did it come to this/ he thought /being such a slut for my big brother, letting him control me, use me like its nothing~/ Sam wept at the thought of waiting to cum, he needed it so bad he didn't think he could hold back long enough. Instinctively Sam humped the air, begging for contact with /anything/ . Dean was right, he was such a desperate whore  
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"Stop" Dean commanded, seeing Sam trying to find friction with his dick, Dean leaned down and grabbed his inner thighs with both of his hands, "I'll take care of that" He said, kitten licking Sam's slit, "Y'know what" Dean said, reaching up and taking off Sam's gag, "I wanna hear your beautiful sounds" Dean says, putting the gag down, "But no talking." He said sternly, getting back to Sam's cock, rubbing it with his right hand  
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Sam's wanton moans while Dean teased him with his tounge and hand made him feel so dirty. He tried his best to resist cumming but he was just so /needy/ and /desperate/ that he couldn't hold back for long. "Mgngm!~ Shit Dean! Fuck!~"  
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Just as Sam was about to cum Dean grabbed the bottom of his cock to make it impossible, "What did I say?" Dean said, "Guess we'll have to so it the hard way" Dean sighed, getting up "Im gonna cum first in your mouth, then your ass and THEN you can cum, if you cum before that, i'll make you cum until you're dry and have nothing left, if you pass out, We'll fuck everyday for a month but everday you'll have a cockring on, okay?"  
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Sam sat up, gripping Dean's arms. "No! No, I-I can't! I need to cum so bad, need it!" Sam begged. "Ca-Can't wait. want-ne need to cum~"  
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"Shut up" Dean said as he slid his cock down Sam's throat forcefully, "You're gonna swallow every last bit of my cum okay?" He said, face-fucking Sam violently, making him gag  
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Sam couldn't answer, so instead  he worked on relaxing his throat so he wouldn't gag as much. He sucked and licked as much as he could, the faster Dean cums the faster he gets to also. The way his brother was basicly forcing his cock in Sam's mouth made him even harder, adding new pressure to his already leaking dick. /What a sight i must be right now, abused lips, hard as a stone, naked and fucked up~/  
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"Sam..." Dean moaned, cumming in Sam's mouth was a nice sight, he carried on thrusting into Sam's mouth lazily, he ripped off Sam's blindfold and pulled out, kissing his used lips and biting down on them, moaning into his mouth, "Change of plan" He says, breathing heavily, Dean took off Sam's cuffs and stared at him, smirking and licking his lips, "Im going to ride you and you're gonna cum in your master's ass, but only after I cum again, okay Sammy? You gonna be a good boy and cum in daddy's ass?" Dean said, "You're gonna eat daddy's ass, stretch him with your fingers so he's ready for your cock, then im gonna ride you"  
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Sam swallowed down Dean's cum and once he was allowed to look at and touch his big brother again he ran his hands over Dean's chest and abs. "Fuck, yes Dean. I'll be a good boy. Fuck you so good, cum in Daddy's ass like a good little slut" Sam alowed Dean to move so he could have access. Sam gave a small lick to the opening of Dean's hole, "So beautiful Daddy" he said, going back to opening Dean up on his tounge, enjoying all of his sweet moans  
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"F-uck" Dean moaned at the wet touch on his ass, "Fuck Sammy faster" Dean said, flopping himself down and biting down on the crappy motel bedsheets, leaving his ass up, he wasn't usually a sub, but when he was he was still a bossy little shit  
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Sam did everything Dean asked of him; faster, harder,/deeper/; until he decided to start streaching his big brother to take his cock. He put two fingers up to Dean's mouth, waiting for him to get them wet. After they were slick enough Sam slowly pushed one finger in, watching Dean moan over the new feeling  
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"Yes Sammy, love those slutty fingers of yours in my pretty ass" Dean moaned loudly as Sam repeatedly brushed over his prostate, "Fuck" He breathed heavily and bucked his hips back, making Sam's big fingers go even deeper, "FASTER!" He commanded, getting impatient  
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"So fucking tight De," Sam shoved a second finger in beside the first one, scissoring and stretching, adding another. He continuously rubbed against Dean's prostate, sending jolts of pleasure through his body. "Fuck Dean, so hot like this"  
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"Sammy please just hurry the fuck up" Dean says, jerking back into Sam's fingers whenever he touched his prostate  
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"Almost done De, you're being such a good boy for me." Sam used his free hand to pet down Dean's back. When he was open enough for Sam he motioned for Dean to sit up. "C'mer, sit on your baby boy's cock Daddy. Ride me so good~"  
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Dean faced Sam and sat on his lap, staring at him he slowly lowered himself onto Sam's cock, taking it inch by inch he finally reached the bottom and let out a breath he didn't know he was holding, "Hold me and kiss me and bite me and praise me Sammy, fuck" He moaned as he moved around, trying to find his prostate and succeeding.  
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"Mhmn, Fuck Dean," Sam moaned when he bottomed out. He pulled Dean's body down to his own, kissing him roughly before moving to his neck. He bit on Dean's collarbone, then sucked a purple hickcy on the mark."God-mhm- so tight De, perfect so perfect for me. Just li-Shit!-like that"  
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"Shut up" Dean said, shoving 2 fingers into Sam's mouth, "Only talk when I tell you to whore" He says aggresively, rocking and pretty much jumping on Sam's cock, needy "F-uck Sam-my~" Dean's toes began to curl, his back started arching back and his mouth was opened wide, eyes were closed and he was full of ecstasy, "Holy shit, fuck you're such a good fucking bitch for me aren't you Sammy?"  
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Sam nodded around Dean's fingers. He sucked at them like it was Dean's cock, running his tounge between them. Sam thrust up into his brother's body, going all the way in every time. "Mn fnna somg!" he moans, words muffled by Dean's makeshift gag  
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Dean takes his wet fingers out, "Wh-what?" Dean asks, now just sitting on Sam's cock, liking the feeling of being so full  
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Sam continued fucking Dean, brrathing heavily. "I-im, shit!- Gonna fucking cum Dean please!"  
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"Cum" Dean simply said, wanting his ass to be dripping Sam's cum and for Sam to be screaming his name  
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Barely after Dean finished the word Sam already came. He shoved roughly against his prostate, a loud and almost-porn-like scream of "Fuck! Deeaan!" on his lips. He took a minute to calm down and enjoy thr view of his brother sitting on his cock. "Look so pretty De- all for me," he said breathy.  
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."Just for you" Dean smiles, getting off Sam's cock and laying down, "Holy shit" Dean says, looking at Sam, slowly going from his messy hair down to his abused lips, his hickey filled neck and shoulders, down to his red chest full of scratch marks and bruises and finally, his beat-out, still leaking cock aling with his bruised thighs, truly a gorgeous sight, Dean could stare forever

**Notes for the Chapter:**

> please please please comment prompts!


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